Covering: 2009 up to the end of 2023Stilbenes, an emblematic group of polyphenols, have attracted the attention of numerous researchers owing to their intriguing polycyclic architectures and diverse bioactivities. In this updated review, natural stilbenes were analysed, especially oligomeric stilbenes, which are an emblematic group of polyphenols that harbor intriguing polycyclic architectures and diverse bioactivities compared with those previously anticipated. Oligomeric stilbenes with unique skeletons comprise a large majority of natural stilbenes owing to their structural changes and different substitutions on the phenyl rings. These compounds can be promising sources of lead compounds for studying new drugs and medicines. In addition, the exploration of unusual structures of oligomeric stilbenes such as polyflavanostilbenes A and B, analysing their absolute stereochemistry, and improving their yield using synthetic biology methods have recently gained interest. This review provides a systematic overview of 409 new stilbenes, which were isolated and identified over time from January 2009 to December 2023, focusing on the classification and biomimetic syntheses of oligomeric stilbenes, in addition to presenting meaningful insights into their structural diversity and biological activities, which will inspire further investigations of biological activities, structure-activity relationships, and screening of drug candidates.